Copertino became the centre of a Contea or County under the Enghiens, who were sovereigns of the land of Galatone, Leverano and Veglie. With the marriage of Mary of Enghien, Countess of Lecce and Copertino (later Queen of Naples and titular Queen of Sicily, Jerusalem, and Hungary), with Raimondo del Balzo Orsini, the county became part of the principality of Taranto. The French knight Tristan Chiaromonte (de Clermont-Lodeve) led the development of the county capital, having assumed power over the territory on his marriage to Caterina, daughter of Mary of Enghien. Tristan's daughter Isabella of Taranto, heiress to the Brienne claim to the Kingdom of Jerusalem, married Ferdinand I of Naples. With the conquest of the Salento pensinsular by the Aragonese dynasty, effected jointly by the Spanish army and knights from Albania, the county was gifted in 1498 to Alfonso Castriota Scanderbeg, in gratitude for military support.
The Princes of Belmonte gained the Castle through the Squarciafico Counts of Copertino, to whom the feudality passed from 1557.